EP0516181A1 - Dérivés de sulfonamide - Google Patents

Dérivés de sulfonamide Download PDF

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Publication number
EP0516181A1
EP0516181A1 EP19920112113 EP92112113A EP0516181A1 EP 0516181 A1 EP0516181 A1 EP 0516181A1 EP 19920112113 EP19920112113 EP 19920112113 EP 92112113 A EP92112113 A EP 92112113A EP 0516181 A1 EP0516181 A1 EP 0516181A1
Authority
EP
European Patent Office
Prior art keywords
group
carbon atom
general formula
heptan
tosylaminobicyclo
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP19920112113
Other languages
German (de)
English (en)
Inventor
Yoshinobu Arai
Nobuyuki Hamanaka
Tohru Dai 2 Minase Haitsu 501 Miyazaki
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ono Pharmaceutical Co Ltd
Original Assignee
Ono Pharmaceutical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP63197180A external-priority patent/JP2565746B2/ja
Application filed by Ono Pharmaceutical Co Ltd filed Critical Ono Pharmaceutical Co Ltd
Publication of EP0516181A1 publication Critical patent/EP0516181A1/fr
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
    • C07C405/005—Analogues or derivatives having the five membered ring replaced by other rings
    • C07C405/0075—Analogues or derivatives having the five membered ring replaced by other rings having the side-chains or their analogues or derivatives attached to a condensed ring system
    • C07C405/0091—Analogues or derivatives having the five membered ring replaced by other rings having the side-chains or their analogues or derivatives attached to a condensed ring system which is bridged condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/20—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms

Definitions

  • the compounds of the general formula (I), of the present ivnention may be prepared by the step described hereinafter.
  • R11' represents an alkyl group of from 1 to 20 carbon atom(s), carbocyclic ring unsubstituted or substituted by an alkyl or alkoxy group of from 1 to 4 carbon atom(s) or halogen atom, or steroid
  • R11'' represents an alkyl group of 1 to 8 carbon atom(s) and the other symbols represent the same meaning as described hereinbefore.
  • Step 1 is the reaction to form amide bond.
  • the reaction may be carried out by reacting (i) with using a corresponding amine shown by the formula H2NR13 (R13 represents the same meaning as described hereinbefore), in an inert organic solvent (methylene chloride, toluene etc), at a temperature of from 0°C to 40°C, after reacting oxalyl chloride, (ii) with using a corresponding amine shown by the formula H2NR13 (R13 represeents the same meaning as described hereinbefore), e.g.
  • step [a] is the introduction of a protecting group (trifluoroacetyl group) into an amino group.
  • a protecting group trifluoroacetyl group
  • it may be carried out with using anhydrous trifluoroacetic acid, in the presence of a tartiary amine (pyridine etc.), in an inert organic solvent (methylene chloride etc.).
  • Step [e] is saponification.
  • it is carried out (i) with using an aqueous solution of an alkali (sodium hydroxide, potassium carbonate, lithium hydroxide etc.), in a water - soluble organic solvent (tetrahydrofuran, methanol, ethanol etc.), or (ii) with using an alkali described hereinbefore, under the anhydrous condition, in an alkanol (methanol, ethanol etc).
  • alkali sodium hydroxide, potassium carbonate, lithium hydroxide etc.
  • a water - soluble organic solvent tetrahydrofuran, methanol, ethanol etc.
  • an alkali described hereinbefore under the anhydrous condition
  • alkanol methanol, ethanol etc.
  • Step [m] is hydrolysis. It may be carried out by reacting with using an acid (hydrochloric acid, acetic acid, oxalic acid etc.), in an inert organic solvent (THF, dioxane, lower alkanol etc.), at a temperature of from 50°C to 100°C.
  • Optical active compounds of the compounds of the general formula (I), wherein represents a group of the formula (Aa-1), (Aa-3), (Aa-4) or (Aa-6) and which have such a configuration that the upper chain (-CH2-Ba-R1) and the lower chain (-NHSO2-R 2a -R 3a ) bond in trans against the ring with respect to each other, may be prepared as follows: 1,3-cyclopentadiene, 1,3-cyclohexadiene, furan or butadiene are reacted with dimenthyl fumarate or menthylmandelyl fumarate in the presence of Lewis' acid.
  • water-soluble salts are preferable.
  • the salt can be isolated by freeze-drying the solution, or by filtration if the salt is sufficiently insoluble to the reaction solution, or if necessary, by removing part of the solvent followed by filtration.
EP19920112113 1987-10-23 1988-10-12 Dérivés de sulfonamide Withdrawn EP0516181A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP266501/87 1987-10-23
JP26650187 1987-10-23
JP197180/88 1988-08-09
JP63197180A JP2565746B2 (ja) 1987-10-23 1988-08-09 新規な炭素環系スルホンアミド誘導体

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
EP88116960.1 Division 1988-10-12

Publications (1)

Publication Number Publication Date
EP0516181A1 true EP0516181A1 (fr) 1992-12-02

Family

ID=26510214

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19920112113 Withdrawn EP0516181A1 (fr) 1987-10-23 1988-10-12 Dérivés de sulfonamide

Country Status (1)

Country Link
EP (1) EP0516181A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2039480A (en) * 1979-01-05 1980-08-13 Jones R Prostaglandins
EP0226346A1 (fr) * 1985-11-18 1987-06-24 Shionogi & Co., Ltd. Dérivés bicycliques de sulfonamides

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2039480A (en) * 1979-01-05 1980-08-13 Jones R Prostaglandins
EP0226346A1 (fr) * 1985-11-18 1987-06-24 Shionogi & Co., Ltd. Dérivés bicycliques de sulfonamides

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